Synthesis of Diversely Functionalized Oxindoles Enabled by Migratory Insertion of Isocyanide to a Transient σ-Alkylpalladium(II) Complex

被引：142

作者：

Kong, Wangqing ^{[1
]}

Wang, Qian ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Synth & Nat Prod, Inst Chem Sci & Engn, EPFL SB ISIC LSPN, BCH 5304, CH-1015 Lausanne, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 33期

基金：

瑞士国家科学基金会;

关键词：

asymmetric synthesis; heterocycles; multicomponent reactions; palladium; synthetic methods; PALLADIUM-CATALYZED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALPHA-ISOCYANOACETAMIDES; MULTICOMPONENT SYNTHESIS; ORTHO-ALKYNYLANILINES; H FUNCTIONALIZATION; CALABAR ALKALOIDS; HECK REACTION; ARYL HALIDES; CYCLIZATION;

D O I：

10.1002/anie.201603950

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium-catalyzed intramolecular carbopalladation of N-aryl acrylamides followed by migratory insertion of an isocyanide-coordinated C(sp(3))-Pd intermediate afforded an alkylimidoyl-PdII complex, which can be intercepted by a nucleophile, including heteroarenes. In addition to amides, the alkylimidoyl-PdII complex was successfully converted into esters, ketones, and bis-heterocyclic compounds. An unprecedented palladium-catalyzed enantioselective domino process involving isocyanide was also documented.

引用

页码：9714 / 9718

页数：5

共 89 条

[31] Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole [J].